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Updated: Mar 20, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Dynamic resolution of 2-cyclohexylidene acetaldehydes through organocatalytic dienamine [4+2] cycloaddition
Jakob Blom1, Tore Kiilerich Johansen, Frank Jensen
1Department of Chemistry, Aarhus University, DK-8000 Aarhus C, Denmark. kaj@chem.au.dk.
Abstract:
Organocatalytic formed dienamines are shown to be involved in dynamic resolution of 2-cyclohexylidene acetaldehydes. By reaction of racemic 2-cyclohexylidene acetaldehydes with benzoquinones in the presence of a diarylprolinol-silyl ether catalyst, tricyclic products are formed in good to high yield and excellent enantioselectivity, while the diastereoselectivity depends on the substituent in the 2-cyclohexylidene acetaldehydes. Studies based on experimental observations and DFT-calculations point to a dynamic thermodynamic resolution-directed pathway. Some transformations of the optically active products are also presented.
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